


On the Subject of Firsts and Awkward I Love You's

by IWannaBeYahtzee



Series: Bedroom Highs [3]
Category: Dear Evan Hansen - Pasek & Paul/Levenson
Genre: Anal Fingering, Anal Sex, Anxiety, Bottom Evan, Cutting, First Time, Fluff, Fluff and Angst, Fluff and Smut, Hair-pulling, Loss of Virginity, M/M, Mentioned: Cutting, Safe Sane and Consensual, Sex, Smut, Top Connor
Language: English
Status: Completed
Published: 2017-12-31
Updated: 2017-12-31
Packaged: 2019-02-24 10:28:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,744
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13211844
Author URL: https://archiveofourown.org/users/IWannaBeYahtzee/pseuds/IWannaBeYahtzee
Summary: Evan and Connor have their first time.It's...weird.It's awkward.And they both make a bunch of mistakes.And it's perfect.





	On the Subject of Firsts and Awkward I Love You's

**Author's Note:**

> So...my first smut..first that I'm publishing anyway...well I hope you like it! I'm pretty satisfied with how it turned out!

Connor had been right in assuming that Evan was very reserved around most people. When it came to PDA Connor couldn't even hold his hand without asking or risk spooking him. When they were alone however it was a different story. He was still a bit hesitant, but much more willing to lean his head on Connor's shoulder or lace their fingers together.

Best of all, when they were alone Connor got to kiss him. He loved kissing Evan, the way he'd melt against him when he nibbled his lower lip. He loved the taste of his shy tongue against his, loved breathing in his earthy scent. Though Connor longed to take things further if all he ever got to do was kiss Evan he would die a happy man.

In fact Connor was immensely surprised that it was Evan who brought up the topic of taking their relationship to the next level.

"Wow. I didn't think _**you'd**_ ever be the one to bring it up."

They had been sitting on Evans couch half watching The Walking Dead cause it was the first thing that came on when they turned on the T.V.

"W-w-w-well I...I see the way you look at me sometimes and I j-just t-think...I mean I like it when you look at me like that I-I kinda wish you would only ever look at me like that but..."

"Evan! Calm down! Take a breath before you pass out!"

Evan took in a breath and let the red drain from his cheeks before Connor spoke again "Look I don't want you to feel like your _obligated_ to do anything-"

"Nono! It's not like that I..." Evan looked down and started fiddling with the edge of his shirt. "...I'd like to. I...I really would I just...I don't think I'm ready yet."

Connor put his arm around Evan and tugged him over until his head was resting on his shoulder. "You don't have to be. Just tell me when you are and we'll go from there? Okay?"

Connor felt Evan nod against his shoulder.

He turned his attention back to the T.V. but neither of them was focusing on the show.

 

  
Evan pulled Connor aside in the hall and spoke to him in hushed tones. "My m-mom's not getting home till late tonight."

"As per usual." Connor replied casually, wondering where Evan was going with this.

"Uhm...i-if you're...uh...I think I'm...r-ready...tonight...m-maybe we could...shit nevermindimsosorryI-"

Connor clapped a hand over his mouth to stop his rambling. He looked around, the hall was mostly empty now. He took his hand away and whispered bluntly "You mean sex?"

Evan turned bright red but he nodded and whispered "Y-yes. I think I'm ready. Are you?"

Connor was blushing too now. "Y-yeah. I'll be there." He walked away, leaving a very red Evan behind him.

  
Connor went straight from school to the drugstore to pick up what he'd need. He wasn't really sure what he was looking for so he just picked up the basics. Condoms and lubricant.

The teenage girl who sold Connor the condoms mentioned his girlfriend was really gonna love these.

"I let that one go. I don't have three hours!" Connor told Evan.

"D-did you get that from Patton Oswalt?"

"...Maybe."

Then Evan laughed.

Connor adored Evan's laugh. He ran a hand through his dark hair and said unsurely "Sooo...should we...take this to the bedroom?"

Evan turned red but nodded. "Y-yeah! T-t-that would be- that would be best!"

Connor let Evan lead him up to his bedroom, CVS bag swinging at his side. Both sat awkwardly on the edge of the bed, trying to figure out where to even begin.

Connor stiffly scooted closer to Evan. "You're sure about this?"

Evan blushed harder and nodded.

"...Okay."

Connor clumsily placed a hand on his chin and pulled him into a kiss.

He tried to focus on the boy in front of him but his thoughts chose then to be especially loud and intrusive.

_"Don't think about it too hard. You're gonna make yourself fuck up. I mean you're probably gonna fuck up anyway, it's your first time. Doesn't everybody fuck up their first time? Well your definitely gonna fuck up cause you fuck up everything."_

But then Evans tongue was brushing up against his and it was hard to think any more. He was getting lost in the kiss. Before he realized it he was lowering Evan to the bed and another thought struck him.

"Wait how do you wanna do this?"

"Huh?"

"I mean do you wanna top or bottom?"

Evan continued to look at him with confusion.

Connor sighed in annoyance. "I mean am I putting it in you or are you putting it in me?"

Evan turned even redder than he already was. "O-oh! Uhhh...T-to be honest I h-hadn't really thought about it! I mean I-I didn't know what you liked and uh uh..."

He chuckled and added "Its okay Evan. While we're being honest with each other..." he blushed and looked away as he said "I don't mind bottoming if you don't want to."

Evan looked like he was considering the offer before looking up at him and asking "W-well what do you want?"

Connor blushed harder and admitted "I always imagined...doing you...when I thought about it."

Evan was very red at this point and was struggling to keep eye contact. "I...I could t-t-try it. W-would it hurt?"

"A bit. At first. I'd have to stretch you out. But it feels really good once you get used to it."

"H-have you...?"

"Just by myself. You?"

"N-never."

He figured as much.

Evan was quiet for moment as he considered his options.

"I...I think I want to try it..."

Connor felt his heart jump into his throat and had to restrain himself from not immediately pouncing on the boy.

"You're sure?"

"...Yeah."

Connor leaned in and captured the blondes lips again in a deep kiss. As Connor nibbled and sucked Evan's lower lip he started pushing the boys shirt up.

Evan stiffened and Connor stopped.

"You okay?"

"I'm fine." Evan replied meekly. He wasn't exactly. There were a million thoughts buzzing around in his skull right now but one was coming through the loudest.

He wanted Connor.

And for once he wasn't going to let his anxiety and his insecurities get in the way of getting that.

He reached for the hem of his shirt but was surprised when Connor stopped him.

"UH-let me."

Evan couldn't help but smirk a little at that.

"What are you? S-some kind of romantic?"

Connor smirked right back at him.

"What can I say? I'm a regular fucking Romeo!"

Evan laughed hard at that and that made Connor chuckle. He wasn't quite so nervous anymore.

Evan sat up long enough to allow Connor to pull his shirt off him. The blonde looked away and tried not to bury himself in the covers. But then Connor was running his hands over his chest and shoulders, which was nice. He leaned down to press kisses into his jaw and neck and reached to tweak at his nipple.

"Ow! W-why...why did you pinch me?"

"Shit! Sorry! I should have asked. I just know that I like it there."

Connors eyes widened and he blushed immediately as if he didn't mean to say that.

Evan smiled incredulously. "R-really?"

"Shut up. Tell you later."

He growled and immediately returned to kissing his neck. He continued to run his hands along Evans chest and stomach, his soft sounds of pleasure encouraging him. The blonde moved to kiss him and wrapped his arms around his neck. Connor could feel the heat rising in his cheeks and arousal coursing through his body.

  
Deep in the moment Connor reached to pull off his shirt. Just for a moment Connor forgot. But then he remembered. And he froze.

Showing Evan his arms was a big deal for Connor. This wasn't going to be the first time. The first wasn't even on purpose. His sleeve had just gotten rolled up without him noticing while they were walking in the orchard and Evan had seen. That day Evan made him promise him to never cut again. When Connor asked him why he was so freaked out Evan showed him a tiny white jagged line at the top of his hip. It was so small and faded it was barely recognizable. Eyes filled with tears and voice choked with shame Evan had told him he wanted to feel numb but he'd chickened out. However in his heightened state of anxiety he was fumbling with the razor and cut himself slightly. It didn't make him feel numb, it only made him feel worse, like he'd even failed at hurting himself. So Connor promised. And despite how hard it got he kept his promise. But that didn't change the fact that the scars remained.

Swallowing he asked "Uh...do you...want me to be naked too?"

Evan nodded without hesitation. "Y-yes...please." Connor wanted to melt. Evan was looking up at him like he was the most precious thing in the world and he just couldn't handle it. He jerked off his jacket and top quickly and got it over with, fighting every instinct that told him to cross his arms over his chest. He put them alongside Evan instead.

  
_"Fuck he's staring. Shiiiit. Now what?!"_

"...your arms."

"For fucks sake Evan! It's not like it's the first time you've seen-"

"No! No! It's j-just-! They're healing! You haven't been...?"

"...No! I...I promised."

Evan's eyes filled with tears but then he smiled and reached up to cup Connor's face in his hand. Connor smiled sadly back before closing his eyes and leaning into his touch. His eyes flew open as Evan pulled him into a shy kiss. He so rarely initiated things like this. He quickly returned it. The kiss quickly turned sensual Connor caressing Evans tongue with his own, encouraging him to play.

The blonde struggled to keep up Connors fast pace, the wet slide of tongue against tongue and the warmth of his partners lips sending shivers down his spine. Connor pulled away and looked into the glazed green eyes of his partner. He thought about putting his hair up as it hung down creating a messy canopy around Evans face but the way the blonde smiled and ran his fingers lovingly through it told him he really didn't mind. He chuckled and murmured "You really like my hair huh? You're always messing with it."

Evan blushed harder and began to stutter. "Oh uh...yeah...I just-"

"Don't apologize." Connor warned. "Its fine. I like it. It feels good."

Evan bit his lip and gave Connor's hair a slight tug. Connor's head drew back slightly with it and he let out a quiet hiss of pleasure. Evan looked up at him expectantly, looking for his reaction.

"Do that again." Connor whispered.

Evan buried his hand in Connor's dark hair and pulled hard. Connor threw his head back. He couldn't help the unrestrained moan that came bursting out of him and he felt a blush rising to his cheeks. Evan flinched and reluctantly drew his hand out of his soft locks. "S-sorry! Was that t-too much?!"

Connor panted and shook his head, smiling down at the blonde. "...No...that was...wow..."

Evan smiled shyly, feeling confident for once. Connor traced the waistband of Evan's khaki's and looked at him for permission. Evan nodded.

"Lift your hips." Connor whispered as he undid the button and zipper. Evan did so and Connor pulled down his pants and underwear. Evan squirmed uncomfortably. He had never been naked in front of anyone before, at least not in a sexual way. Still he tried his best to keep his hands at his side's but then that felt weird because who keeps their hands glued to their side's during sex? And-

"Evan?"

The blonde was brought out of his own head by Connor's concerned voice. He liked Connor's voice. It was so much softer than it was around other people.

"Y-yeah?"

"Do you wanna stop? You seem really uncomfortable."

"No! I- it's...it's not that I just...I have no idea what I'm doing. I've never done anything like this and I just don't wanna screw up and ruin it and-"

"Evan. First of all, neither do I. I've just seen enough on the internet to know what I'm into. Second, me neither. Closest I've ever gotten is an ex dealer forcing his tongue down my throat and me knocking his teeth out. Third, we're both probably gonna screw up, it's our first time, its gonna happen. But you're not gonna ruin it. I promise."

Evan smiled. Connor said he wasn't good at comforting people and most of the time...he really wasn't. But every now and then he knew just what to say.

When he finally got a good look at Evan he couldn't help but whistle wolfishly. He was beautiful. Evan couldn't help but blush and cover his face at Connor's behaviour beaming all the while. As Connor ran a hand along the blonde's thigh he saw it again.

That tiny white scar. He traced it carefully as Evan peeked over his fingers before turning away in shame, tears pricking his eyes. Connor ran his lips along the tiny white scar and attempted to comfort the blonde.

"I'm such a baby!"

Evan whimpered quietly as he tried to relax.

"No you're not."

Connor murmured, gently pecking him on the lips and thumbing away his tears.

"You okay?" Connor asked.

"Yeah." Evan whispered, gently brushing his cheek in thanks. Connor continued to rub at his thigh before gently brushing his erect cock. Evan gasped and whimpered softly as Connor continued to stroke him experimentally. "That feel good?" Connor asked. Evan nodded fervently. "Y-yeah! It's good!" He cried. Seeing that Evan was enjoying it he gripped him a little more firmly and caressed the head with his thumb, becoming a bit bolder in his movements. Connor wasn't really sure what he was doing but he found that it wasn't too different from pleasuring himself and the way Evan was reacting only spurred him on.

Evan reached out and touched the button of Connor's pants. "Connor I...I..." He blushed as he trailed off. "What is it?" Connor murmured. He was being a bit mean, he knew it. He knew what Evan wanted, but he wanted to hear him say it. Evan bit his lip and fiddled with the button of his jeans. "I...I w-want to t-touch you too..." He whimpered. Connor smiled fondly down at him. "Go ahead." He whispered. Evan undid his jeans and pulled Connor out of them. He started to stroke him at an uneven pace, probably because his nerves were starting to catch up with him. Connor took his hand and steadied him. He panted and groaned lowly at the friction and warmth of Evan's fingers. Evan licked his dry lips and stuttered out "C-can I...can I s-suck it?"

"Oh hell yes!" Connor cried.

Nerves aside, Evan couldn't help but smile at his reaction. Connor sat up and tugged his pants and underwear the rest of the way down, tossing them off the bed. Evan bent and tentatively licked him at the tip. Blushing furiously, eyes squeezed tight, he slowly took in the head and sucked gently. Connor gasped and raked his fingers across his blonde hair. Evan began to bob his head inexperiencedly, relishing the taste of Connor's skin on his tongue.  
Connor hissed slightly as Evan nicked him. "Ah! Little less teeth, Ev?"

Evan pulled off and cast his eyes to the sheets. "S-sorry! D-did I hurt you?" Connor caressed his hair comfortingly. "Your fine, Evan. It feels really good. Please keep going." Evan nodded. He hesitantly licked up the base and took him back into his mouth, this time making sure to watch for his teeth. He bobbed his head arrhythmically trying to find a good pace. Connor groaned "Ah Ev! That's...good! C-Could you...touch my balls a little too?"

Evan reached underneath him and tenderly cupped his testicles, fondling them gently. He could feel how hot and heavy they were. Connor cried out in ecstasy, arching his back. He could feel his orgasm approaching, he wanted to come so badly but he also wanted him and Evan to come at the same time. "Evan! Stop!" He gasped, pulling the blonde off of him. "What is it? D-did I hurt you again?"

Connor shook his head. "I'd have come if you didn't stop."

Evan smiled and pulled him into a kiss. Connor could taste himself on Evans lips and it only turned him on more.

"So..." Evan murmured hesitantly. "Now we..."

"Yeah." Connor replied. "If you still want to."

"No I do." He took a deep breath, reached into the plastic bag on the bedside table and pulled out the lubricant. "S-so d-do we-? H-how do we-?"

Connor carefully took the tube from Evans hand. "Uh here. Just let me."

He spread Evans legs, maybe just a bit too roughly as impatience was taking over him and his cock was screaming for relief. He slipped in between his legs, uncapped the tube, spread a good amount onto his hand and warmed it between his fingers. Evan took in a deep breath and tried to relax his body as much as he could. He felt Connor's fingers at his hole and he tensed.

"Evan you have to relax." Connor soothed as he gently traced circles around the tight skin of his opening. Connors gentle ministrations slowly began to ease the tension in his muscles until he was lax enough to allow him to slip a finger in. Evan gasped and tried not to tighten up.

"You okay? Does it hurt?" Connor asked.

"I-I...I don't know...it feels weird!" Evan whimpered. Connor gently flexed his finger and Evan cried out as a slight burning sensation filled him. It wasn't pleasant but it was bearable as Connor slowly continued to stretch him. Evan became aware that Connor was prodding steadily at different spots inside him, almost as if he was looking for something. Evan was just about to ask what he was doing when he felt a rush of what felt like electricity run up his spine and pleasure pool warmly into his stomach. His toes curled and he cried out in surprise and bliss. Opening his eyes again he saw Connor smirking, triumphant. "Found it."

Now Evan knew what a prostate was. His mother was a nurse, it was kinda hard NOT to know what it was. He just didn't know that the prostate could feel like...that. Connor seemed to pick up on his confusion. "Have you ever fingered yourself before?" He asked.

He shook his head.

"You uh...didn't know about...this?" He pressed against the spot again.

Evan gasped before he answered "I k-knew! I j-j-just didn't know that it f-felt like that."

"You like that?" Connor teased, deliberately rubbing against the little bundle of nerves. Evan cried out and whimpered, arching his back and trying to push the digit deeper inside him. "Aaah! Yes! I...I..."

Connor smirked and pushed another finger in. Once again the stretch burned but Connor's gentle scissoring and caressing of his inner walls filled him with tingling pleasure. Connor licked up his chest and sucked a bruise into his collar bone, utterly lost in his body. Evan threw his head back and moaned, bucking his hips against the older boys fingers impatiently. He was beginning to enjoy the filling sensation inside him and he wanted more but he was still too embarrassed to ask for it. When Connor finally pushed a third finger in, he cracked.

"C-Connor! T-that's enough! I'm...ready." He whimpered, blushing down to his shoulders. Connor pulled away from Evans neck and sat back to look at him. Flushed, forest green eyes glazed and full of longing, naked and hard in front of him. Connor had to take a breath and remember this was real.

"You really want me?" He asked, smiling fondly down at him.

"Y-yeah I do." Evan replied, gladly returning the smile.

Connor felt a wonderful warmth in his chest and he pulled Evan into his arms and kissed him hard. He fumbled with the condom wrapper because his hands were slippery with lube. "Uh do you w-want me to-?" Evan asked holding out his hand. Connor sighed through his nose and handed over the condom. Evan opened it and started to hand it back to Connor but he stopped him. "Do you wanna put it on for me?" Evan blushed again and swallowed hard before gently rolling the condom over Connors hard cock. He took the lubricant off of the bedside table and gently stroked it onto him. Connor bit back a groan and roughly whispered "That's good." gently brushing his hand away.

He wrapped Evan legs around his waist and positioned himself. He looked up at him and interlaced their fingers.

Evan looked nervous but he smiled up at him. "I trust you, Connor."

Connor smiled back and pushed in. He was about halfway in before Evan had to ask him to stop and wait for him to adjust. The stretch, the burn, the filling sensation, it was all too much. Finally he was able to relax and Connor was able to slide himself all the way in. Evan keened at the overwhelming feeling, pain and pleasure swirling together in a sensation he'd never experienced before.

Connor had never been good at impulse control. But now his face was buried painfully hard into Evans neck and his hips trembled with effort not to move inside of Evan.

The blonde buried his hands into that messy raven mop and tried to focus on the pleasure slowly building in him. Connor shuddered above him and whispered "Ffffuck Evan! Y-you're so...tight!" He felt him throb and he had to bite back a whimper.

"You can m-move! It's not as b-bad as it w-was before." Evan gasped. Connor pulled his hips back just a bit before thrusting back in. Evan softly moaned as Connor thrust shallowly, trying to find his rhythm, gradually picking up speed. Bliss was steadily building with every snap of his hips.

"How do you...feel?" Connor asked breathily.

"Hot! F-full!" Was all he could manage. The hot pull of skin and the agonizingly sweet sensation of being filled was setting a thick cloud over his mind. Connor pressed his forehead against Evan's and groaned, digging his nails into the blondes hips. "You feel so fucking good!" He hissed, giving a particularly hard buck of his hips and drawing a loud cry out of Evan.

"Aaah! There! C-Connor!"

"I seem to have a talent for finding that!"

"Shut up! Cocky bastard!"

Connor picked up the pace, pounding against that little spot, making Evan tremble as waves of ecstasy rolled through his body. Connor could feel his walls spasming around him and whimpered desperately as pleasure filled his every nerve. Evan began to buck his hips up to meet Connors thrusts, completely lost to the bliss of the meeting of bodies, the feeling of skin on skin. Connor knew he wouldn't last long at this point. "Fuck! Ev, I'm close already!"

Evan wanted to feel it. He wanted to feel that spill. To feel his warmth pouring inside him.

"Oh god! Connor! Cum in me!"

"You want me to take this off?" Connor slowed and placed his fingers where they were connected, fingering the edge of the condom.

"Yes! Please! Cum in me please!"

Connor quickly pulled out, took off the condom and tossed it away and thrust back in. Evan nearly screamed, tears filling his eyes, every pump pushing him further towards the edge. Connor leaned down and whispered huskily in his ear "You close Ev?"

Evan nodded eagerly.

Connor just kept talking, not having any experience with dirty talk, not really aware of the pure filth coming out of his mouth.

"You feel so good! You're so beautiful! I'm so fucking close! I'm gonna come inside you!"

  
And if that wasn't the most erotic thing he'd ever heard. Evan wrapped his arms around him, clutching his hair, holding on for dear life.

"I love you! I! LOVE! YOU!" Evan cried.

  
Neither of them really registered what what he had just said would mean for them. Right now all that registered was good and right and yes. Connor gritted his teeth as he felt his orgasm approaching. "Cumming!"

And then Evan felt it, that hot rush inside him he had been waiting for. The warmth gushing inside him tipped him over the edge and he came with Connor's name on his lips. When he came back to himself Connor was still inside him, laying on top of him as they both caught their breath. Just when he'd got it again Connor leaned up and kissed him and took it away again. He broke the kiss and finally pulled out, making Evan gasp at the sudden empty feeling inside him. He gasped again when he felt Connor's cum trickling down his thighs. Evan felt a bit of his anxiety coming back to him as he started to question whether removing the protection was truly a good idea. Seeming to read the uneasiness on his face Connor soothed him. "Relax. We're both clean. And it's not like you can get pregnant."

Connor laid down next to him. Evan took a breath and let it out slowly. Connor was right. There was nothing to worry about. Evan snuggled up to him and felt his eyes begin to droop.

"That was fucking awesome." Connor stated.

Evan smiled and snickered. "Yeah. That was...really nice." He blushed and buried his face into Connors neck. His smile faded just a bit.

"Connor a-about what I said..."

Connor turned his chin towards him and kissed him.

"Talk about it later. Sleep now." Connor smiled fondly down at him. Evan nodded and they did just that.

 

When Evan sleepily came down the stairs the next morning, Connor a few steps behind him, Heidi was waiting for them at the kitchen table with coffee. "Well good morning sleepyheads! Connor Hi! I didn't know you were staying the night!"

Not a word needed to be exchanged between the two to know that the current plan was: play dumb.

"I-I meant to text you." Evan stuttered guiltiliy.

"Oh it's fine sweetheart! You know I love having Connor over as much as you do!" She said waving her hand dismissively.

 _'Well maybe not quite as much.'_ Connor thought.

"Nice to see you again Mrs Hansen."

"Oh sweetie, how many times do I have to tell you to call me Heidi?" She teased grabbing her purse. "Well I have to go, they need me early today, you boys can handle breakfast right?"

"Yup."

"Yes mom."

"Good. Love you sweetie. Bye." She kissed Evan on the forehead and gave Connor a quick hug before leaving. Connor couldn't help but smile. "Your mom is...really awesome."

Evan smiled awkwardly. "...She tries."

"At least she does that."

Evan set about making himself some toast while Connor poured himself a bowl of cereal.

"Are you gonna tell her...about us?" Connor asked.

"....eventually."

That was code for "no time soon if I can avoid it."

Connor could understand that. He was in no hurry to come out to his parents though he was pretty sure they already knew. But there were his intrusive thoughts again, telling him that the real reason was that Evan was ashamed of a pothead, scar armed, scary looking motherfucker like him. But he knew that wasn't true. Heidi loved having him around, she'd just told him so, and Evan...Evan had just given him his virginity. He had trusted him with a gift, a part of himself he had never shown to anyone else. That had to mean something. He hadn't even realized he was staring with a big adoring smile on his face until Evan turned from the toaster and asked him "W-What?"

Connor answered honestly. "Just thinking about how much I love you."

Evan's entire face turned red. "O-oh. I uh- good! I l-love you t-too!" He stuttered before turning back to his toast. Connor smiled and started eating his cereal.

**Author's Note:**

> Sooo...was it good for you? Don't forget to comment, comment, comment! And if you really liked it maybe give me a kudos and a bookmark!


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